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STATE PLANT BOARD 

September 1953 E-863 

United States Department of Agriculture 
Agricultural Research Administration 
Bureau of Entomology and Plant Quarantine 



LABORATORY TESTS OF SOME ORGANIC COMPOUNDS AS INSECTICIDES 



By G. T. Bottger and A. P. Yerington, 
Division of Insecticide Investigations 



A total of 237 organic compounds has been received from the Chemi- 
cal-Biological Coordination Center, of the National Research Council, and 
tested as insecticides at the Anaheim, Calif., laboratory of this Bureau. 
In this report are included the results obtained from tests made from 
November 19^9 through December 19!?2. 

The compounds were all given initial tests as 10-percent dusts or 
5-percent acetone sprays against at least three species of insects. 
Spider mites were sprayed at either 1- or 5-percent concentrations. When- 
ever time permitted, materials that had given mortalities of 10 percent 
in the initial test were retested at reduced concentrations. 

The following species were used: 

Armyworm ( Pseudaletia unipuncta (Haw.)) 

Celery leaf tier ( Phlyctaenia rubigalis (Guen.)) 

Citrus red mite ( Metatetranychus citri (McG.)) 

Large milkweed bug ( Oncopeltus fasciatus (Dall.)) 

Pea aphid ( Macrosiphum pisi (Harris)) 

Two-spotted spider mite ( Tetranychus bimaculatus Harvey) 

All species of insects were reared in the laboratory; the citrus and 
two-spotted mites were collected in the field. Larvae of the lepidopter- 
ous insects were placed in petri dishes with foliage that had been dusted 
or sprayed with the compounds. Aphids were dusted or sprayed either on 
or removed from the plant, and were confined during the test period on 
potted Windsor bean plants in cloth-capped glass battery jars 7 inches in 
diameter. The two-spotted spider mites were always dusted while on castor 
bean leaves and were then kept in battery jars. 

Both active and egg stages of the citrus red mite were treated by 
dipping infested oranges into the insecticide. Milkweed bugs were dusted 
or sprayed while confined in 9-cm. crystallizing dishes in which they were 
retained during the test period. 

In the tests with lepidopterous insects 30 larvae were used per test; 
a minimum of 20 milkweed bugs were used, and the number of aphids and 
mites ranged from around this minimum to several times this number. The 
test period was usually 1 day for aphids, 2 days for other insects, and 
2 or 3 days for the mites. 



- 2 - 

onds thai tested as dusts were dilut* .lite, 

were in rood physical 

For comparative purposes tests w* b Arandte, lindane 

and parathion. The results of the dust tests *.hree 

chown in table 1. Results of the spray t< -or 

standards are shown in table 3. 

Data on 15 organic compounds that caused more than 7li percent rr.r i 
tality to one or more species of insects in dust tests are shown in tar 
2. Of these compounds h were effective against the ar :.st 

the pea aphid, and 10 against the two-spotted spider mite. None of the 
compounds was effective against more than one species and the only con- 
pounds that continued to cause hich kills at reduced concentrations 
li-(l,3>3,3,-tetrachlorcpropyl)cyclohexene and 3-vinylpyridine . 

Data on 75 compounds that caused more than Ih percer.' to 

one or more species of insects in acetone spray tests are she-* 
L. Of these compounds 2li were effective against the arrv.-v r~. , 11 agair. 
the large milkweed bug, 32 against the pea aphid, 62 i t the citrus 

red mite, and 5 against the two-spotted spider mite, ^nly 7 of the compounds 
shown in this table were tested against ". - 'ted spider mite. 1- 

(2-chloroethyl)-2-(p_-chlorophenoxy) ethane and trichloronethane 
acid diethyl ester were effective against all h species when used at con- 
centrations of 5 percent. However, when the concentration of the latt- 
compound was reduced to 1 percent in tests a" the amyworra and the 

pea aphid, low mortalities resulted. Phosphorous acid diethyl p-nitro- 
phenyl ester was the most effective material tested. It caused high mor- 
talities of armyworms and pea aphids when used at concentrations of C.C©5 
percent. Ethyl chlorophosphate I Lvs against the citrus mit» 

used at a concentration of 0.001 percent. Compared with citrus mite mor- 
talities resulting from the use of the standard materials, et 
phosphate was roughly 20 times as effective as Aramite and 2.5 tines as 
ective as parathion. 

The lli7 compounds that i less than 75 perc -he 

species tested are listed in t L7 of I iused - 

50-percent mortality to one or more of the insects tested. -m- 

pounds vera aniline complex with T f*vt« C lldc acid, I 

acid butyl ester; 2,3-dihydrc .ylbenzofuran; cvclohexyl amine corap' 

tfa \ f.w . f] IO( I Hole acid; and \ were I 

pea aphi:: r '.r , .)• 

, which was nst the pea inc the a m t 

and 2 /2- (2- . nopropox;. QOl, which was I ! .ve 

against t: i aphi<: he citrus Bite; 

ich was si against the 

rbonic acid, di benzyl estSTj 
itrof nic acid , 

anol; Lc aci 

yl) s tear amide, - were fff*»ctive 

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Table 5. — Compounds causing less than 7S> percent mortality of any species 
of insect fed dusted or sprayed foliage. Ten percent dusts, 5 percent 
acetone sprays, unless indicated otherwise. 



£-Acenaphthenecrotonic acid, ct-oxo- 

Acetic acid, trifluoro- 

dl -Alanine, N-(2-cyanoethyl)- 

dl -Alanine, N,N-bis(2-cyanoethyl)- 

Allyl sulfate, mono-, sodium salt 

Ammonium chloride, (x-kerylbenzyl)- 

trimethyl- 
Aniline, complex with | f.wt. fluo- 

silicic acid 
dl-Aspartic acid, N-(2-cyanoethyl)- 
dl-Aspartic acid, N,N-bis(2,cyanoethyl)- 
p_-Benzenediacetic acid, 2,5-dihydroxy- 
Benzenesulfonic acid, butyl ester 
Benzenesulf onic acid, x- sec -butyl-, 

phenyl ester 
Benzenesulfonic acid, diester with 

diethylene glycol 
Benzenesulfonic acid, ethyl ester 
Benzenesulfonic acid, ethylene diester 
Benzenesulfonic acid, propyl ester 
Benzofuran, 2,3-dihydro-2-methyl- 1/ 
Benzofuran, 3>6-dimethyl- 
Benzonitrile 
9,9'-Bianthryl 

Butyric acid, allyl ester 1/ 
Butyric acid, l-(2-benzyloxy- 

carbethoxy) ethyl ester 
Butyric acid, (X -hydroxy- <A-methyl-l/ 
Carbonic acid, bis(o-chlorobenzyl) ester 
Carbonic acid, dibenzyl ester 
Carbonic acid, bis(2,li-dichloro- 

benzyl) ester 
Carbonic acid, bis(2,li-dimethyl- 

benzyl) ester 
Carbonic acid, bis(x-isopropyl- 

benzyl) ester 
Carbonic acid, bis(/tri(and tetra) 

methylbenzylj ester 
Chalcone , 3 9 ii-me thylenedi oxy- 
(X -Conidendrin 
3 -Conidendrin 
/$ -Conidendrol 
c{ -Conidendrol, dihydrate 



Cornstarch, tri-o-chlorophenyl- 

carbamate, polymer 
Coumarin, 3-acetyl-8-methoxy- 
o-Cresol, 6-allyl- 
Cyclohexane, cis(and trans ) -1,2- 

dichloro-ii- ( 1 , 2-dichlor oethyl) - 
1 , li-Cyclohexanediol 
Cyclohexane, 1,2,4,5-tetramethyl 1/ 
Cyclohexane, 1,2,4-triraethyl- 1/ 
Cyclohexvlamine , complex with 

\ f.wt. fluosilicic acid 
Diamidophosphoryl chloride, 

tetramethyl 1/ 
1,2 -Ethane diphosphonic acid 
1,2-Ethanediphosphonic acid, 

tetraethyl ester 
Ethanol, 2-^2-^2-(3-aminopropoxy)- 

ethoxy]ethoxyJ- - 
Ethanol, 2-(2-chloroethoxy)- 
Ethanol, 2-(2-dimethylamino- 

ethoxy) - 1/ 
Ethanol, 2-(2-ethoxyethoxy)- 

2,2 , -iminodi, complex 
f.wt. fluosilicic acid 
2 -i s opropoxy- 
2-( 2-isopropoxyethoxy) - 
2-methoxy- 
Ethanol, 2-( 2-methox7ethoxy)- 
Ethanol, 2,2' ,2"-nitrilotri T , 

complex with \ f.wt. fluo- 
silicic acid 
Ethyl chlorothiophosphate 1/ 
Fur an, 2-methoxymethyl-5>-nitro- 
Furan, 2- [2-(2,i;,6-trinitro- 

phenyl) -vinyl ]- 
d-Glucoside, d-allyl- 
1-Glutamic acid, N,N-bis(2- 

cyanoethyl)-, monohydrate 
1-Glutamic acid, N-(p_-nitro- 

phenylsulf onyl ) - 
1 -Glutamic acid, N-(sulfanilyl)- 
Glycocyamine 
Guaiacol, 6-allyl- 



Ethanol, 
with \ 
Ethanol, 
Ethanol, 
Ethanol, 



1/ One-percent acetone spray used against citrus mite. 



Table 5. — (Continued) 



- 24 - 



•i6, complex witn g f.wt. 

fluoailicic ae 
Indan, x,x- : ichloro-l f 1 , 3-tri- 

methyl -3- phenyl - 
Indole, 2-(p_-chlorophenyl)- 
Iodonium chloride, bis(p_- 

chlorophenyl)- 
Iodonium chloride, bis(o^- 

iodophenyl)- 
I odonium chloride, diphenyl- 
Iodonium iodide, bis(£-chlorophenyl ) - 
I odonium iodide, bis (p_-iodophenyl)- 
I odonium iodide, diohenyl- 
I odonium sulfate, bi s(p_-chloro- 

pher.yl)- 
Iodonium sulfate, bis(p_-iodophenyl)- 
; mium triiodide, iiphenyl- 
•. ic acid, acetate, p- tert- 

butylphenyl ester 
tic acid, acetate, diest r 

with trie thy lene glycol 
Lactic acid, acetate, 2-(2-eth. - 

hexylox.y) ethyl ester 
Lactic acid, acetate, hcxa 

es - 

ic acid, allyl ester 
Lactic acid, tetrahydrofurf uryl 

ester, hydrogen carbonate, di- 

ester with diethylene glycol 
1 -Leucine , N- ( 2-cyanoethyl)- 

'leanilide, dimer 
• Leio aoid , d 

etl. 1 lactate 

ieic acid, diester with 2- 

ethylhexyl lactate 
Malonic acid, allyl-J/ 
Malor.ic acid, methylene-, 

.'.,•■ 
lietanicotine 
di-Lin' - -oyanorthyl)- 

Hor l.wt. 

:ic acid 
Naphthaleno, 1 , b-<l imcthoxy- 
id, amyl eat 

ester 

eater 



tinic acid, hexyl es - 
. d, octyl of 
ide 
Pelargonic acid, ester w 
allyl lactate 
• r oione 
Phenol, o-allyl- 

alic acid, die3ter w I 
.lbutyl lac* 
Piperidine, 4,4'-ethylenedi- 

- -opanol, 1-buto I - 
2-Propanol, l-(-:-cyclohexylphe:. 
2-Frc r ancl, 2,2'- - - -rrcplex 

wi*. .wt. fluosilicic acid 

2-Propanol, 1-r -, acetate 

Propionic aoid* fl-ie 
de cy 1 e 8 * 
. :l..e, 2,6-d;ctyryl- 
Pyridine, 4, 4 ' -ethyl m ■ 

dine, 4,4' ,4"-glycer. 
Pyridine, 3-(hycroxymercuri)-, 

stearate 
Pyridine, 4,4'-vinylene d - 
Py r imi di: • , -.,'..,--*•' kf I . D - , 
monosul :'ite 

, 2 , 5 , f - -, 

monosulf ate, monohydrate 

• amic acid, '. - . - anoethyl)- 

, 2— -e* 
Salicyclic acid, ethyl estor. 

diester with cathonic acidi/ 
Sesamol 
Stearamide, B- 

\ramide, N-(ethoxyaethyl)- 
Stei )- 

Ste '.'- ( i aopropoxymethyl)- 

Stearamide, K-(rnet 

••thylenel 

• . I - voctyloxymethyl)- 
Stearami- - eb:s- 
Stearamide. ?.,V-- -.'.<-:. \ l<v.ebi a- 

. ' ■ . • ■ - 

Ste.v ", N,N'- . - - 

Stearar 
4,4' "_- J> r.idide 

lyl- 
■tthyft- 



- 25 - 



Table 5. — (Continued) 



Sulfide, ethyl phenyl 

Terephthalic acid, bis(2-ethylhexyl) ester 

Thiocyanic acid, x-kerylbenzyl ester 

Toluene, CL-chloro-x-keryl- 

m-T o 1 uni t ri le 

o-Tolunitrile 

p-Tolunitrile 

T-Tyrosine, N-(2-cyanoethyl)- 

Uric acid 

Xanthic acid, sec -butyl-, sodium salt 

Xanthic acid, isopropyl-, sodium salt 



3 1262 09239 6190